ZA200302554B - Novel polymorphic form of 17-beta-(N-ter.butyl carbamoyl)-4-aza-5-alpha-androst-1-en-3-one and a process for preparing it. - Google Patents
Novel polymorphic form of 17-beta-(N-ter.butyl carbamoyl)-4-aza-5-alpha-androst-1-en-3-one and a process for preparing it. Download PDFInfo
- Publication number
- ZA200302554B ZA200302554B ZA200302554A ZA200302554A ZA200302554B ZA 200302554 B ZA200302554 B ZA 200302554B ZA 200302554 A ZA200302554 A ZA 200302554A ZA 200302554 A ZA200302554 A ZA 200302554A ZA 200302554 B ZA200302554 B ZA 200302554B
- Authority
- ZA
- South Africa
- Prior art keywords
- aza
- androst
- ter
- butyl carbamoyl
- iii
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 239000003208 petroleum Substances 0.000 claims description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkyl acetates Chemical class 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 239000003495 polar organic solvent Substances 0.000 claims description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 238000007796 conventional method Methods 0.000 claims description 5
- 238000009738 saturating Methods 0.000 claims description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 239000007787 solid Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 12
- 229960004039 finasteride Drugs 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- LYQLGOGKDQKQAX-OJEXMJBDSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 LYQLGOGKDQKQAX-OJEXMJBDSA-N 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 description 1
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011165 process development Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
- C07J73/005—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/28—Antiandrogens
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN737DE2000 | 2000-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200302554B true ZA200302554B (en) | 2004-02-19 |
Family
ID=11097081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200302554A ZA200302554B (en) | 2000-09-07 | 2003-04-01 | Novel polymorphic form of 17-beta-(N-ter.butyl carbamoyl)-4-aza-5-alpha-androst-1-en-3-one and a process for preparing it. |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1322663A1 (no) |
| JP (1) | JP2004508380A (no) |
| AU (1) | AU6991101A (no) |
| BR (1) | BR0113732A (no) |
| CA (1) | CA2422159A1 (no) |
| HU (1) | HUP0300937A3 (no) |
| IL (1) | IL154785A0 (no) |
| NO (1) | NO20031045L (no) |
| NZ (1) | NZ525116A (no) |
| PL (1) | PL361014A1 (no) |
| WO (1) | WO2002020553A1 (no) |
| ZA (1) | ZA200302554B (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2206065B1 (es) * | 2002-10-31 | 2005-08-16 | Ragactives, S.L. | Procedimiento para la obtencion de la forma polimorfica i de finasterida. |
| EP1651661B1 (en) * | 2003-07-03 | 2008-08-27 | Cipla Ltd. | Process for the preparation of finasteride form i |
| CN1294913C (zh) * | 2004-12-23 | 2007-01-17 | 鲁南制药集团股份有限公司 | 含有非那雄胺与环糊精或其衍生物的药物组合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ225100A (en) * | 1987-06-29 | 1991-09-25 | Merck & Co Inc | Reaction of steroids (including 4-azasteroids) with a silylating agent in the presence of a quinone to introduce a delta' double bond and silylated intermediates |
| US5237061A (en) * | 1988-10-31 | 1993-08-17 | Merck & Co., Inc. | Methods of synthesizing benign prostatic hypertropic agents and their intermediates |
| US5021575A (en) * | 1989-11-13 | 1991-06-04 | Merck & Co., Inc. | Method for introducing a 1,2 double bond into azasteroids |
| US5091534A (en) * | 1990-08-27 | 1992-02-25 | Merck & Co., Inc. | Trialkylsilyl trifluoromethanesulfonate mediated α-methylenic carbon functionalization of 4-AZA-5α-androstan-3-one steroids |
| US5468860A (en) * | 1992-11-19 | 1995-11-21 | Merck & Co., Inc. | New finasteride processes |
-
2001
- 2001-06-19 JP JP2002525173A patent/JP2004508380A/ja not_active Withdrawn
- 2001-06-19 BR BR0113732-8A patent/BR0113732A/pt not_active Application Discontinuation
- 2001-06-19 WO PCT/US2001/019546 patent/WO2002020553A1/en not_active Application Discontinuation
- 2001-06-19 CA CA002422159A patent/CA2422159A1/en not_active Abandoned
- 2001-06-19 HU HU0300937A patent/HUP0300937A3/hu unknown
- 2001-06-19 PL PL01361014A patent/PL361014A1/xx not_active Application Discontinuation
- 2001-06-19 IL IL15478501A patent/IL154785A0/xx unknown
- 2001-06-19 EP EP01948467A patent/EP1322663A1/en not_active Ceased
- 2001-06-19 NZ NZ525116A patent/NZ525116A/en unknown
- 2001-06-19 AU AU6991101A patent/AU6991101A/xx active Pending
-
2003
- 2003-03-06 NO NO20031045A patent/NO20031045L/no not_active Application Discontinuation
- 2003-04-01 ZA ZA200302554A patent/ZA200302554B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0300937A2 (en) | 2007-02-28 |
| NZ525116A (en) | 2004-11-26 |
| CA2422159A1 (en) | 2002-03-14 |
| WO2002020553A1 (en) | 2002-03-14 |
| BR0113732A (pt) | 2003-07-29 |
| HUP0300937A3 (en) | 2007-10-29 |
| NO20031045D0 (no) | 2003-03-06 |
| JP2004508380A (ja) | 2004-03-18 |
| PL361014A1 (en) | 2004-09-20 |
| EP1322663A1 (en) | 2003-07-02 |
| NO20031045L (no) | 2003-04-29 |
| AU6991101A (en) | 2002-03-22 |
| IL154785A0 (en) | 2003-10-31 |
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